Caught!
by Davidk92
Summary: Tails is caught trying on Amy's clothes while she's on vacation. What will Amy do to the poor fox? Read and find out.
1. Amy's Vacation

Tails propped his feet up on Amy's coffee table, a can of Coke in his hand. Said pink hedgehog wasn't around, as she had gone on a holiday or a week and left the unnaturally responsible 8-year old to watch her house for her. It was currently day 3 of Amy's vacation, and Tails was making sure nothing happened.

"Ah…" he sighed, reclining into her couch. "This is great! I can get to see what it's like to have a house to my own!" Tails took a sip from his can. Yep, he had the place to himself. He could do whatever he wanted. The only thing Amy had forbidden him to do was go into her room. Tails glanced up at her door.

Perhaps he could take a look. Amy wasn't here. No, no, what was he thinking? The fox couldn't abuse Amy's trust like that. But she'll never know, said a small voice in his head. Go on, she won't mind you just taking a quick look, will she?

Tails set his Coke down. That's right, he had four days until Amy came home, and how will she know he's been in her room? Tails went upstairs and slowly opened the door.

Pink. Amy's room was bright pink, with pictures of her, Cream and Sonic everywhere. Tails walked in cautiously. He had never been in a girl's room before, and he accidentally stubbed his toe on a chest off drawers. After recovering from the pain, he looked hard at it. Like the rest of the room, it was pink, but Tails had never seen a girl's clothes drawer before, and decided to take a look.

Opening the bottom drawer, the kitsune found Amy's underwear drawer. Picking out a pair of panties at random, Tails lifted them up and took a good look at them. A soft pink colour with frills on the edges was what he saw, and he began thinking "Why in the world do girls wear these? Don't those frills itch? And why is it so fancy? No one's going to see them?" Only one way to find out, said that voice in his head again. What? No! This was just plain stupid! He couldn't try on Amy's clothes!

Could he? He did wonder what they felt like. And they looked so soft…. Tails began to take off his gloves and shoes.

Elsewhere, a certain pink hedgehog was on a taxi home. She had cut her break off early, unable to bear being away from her Sonikku for so long. And all the others thought she was still on her trip; Amy couldn't wait to surprise them!


	2. Caught In the Act

Tails had discarded his gloves and shoes, and slipped the panties up his legs and over his crotch. Tails, to his surprise, enjoyed the feel of Amy's silky underwear. He began looking through her drawer trying to find something else.

Amy glanced out of the taxi's window, seeing her street.

"Stop here," she ordered, and the driver complied at the corner. "Thanks, I'll walk it from here." She glanced at the fare, and saw it said £4.50. "Here's a fiver, keep the change." she said handing a five pound note to the driver, before heading down the street with her suitcases in her hands and camera hanging around her neck.

Tails looked at himself in the mirror. He had been able to find a matching bra with a white floral pattern, and had currently stuffed it with some tissues, giving him some breasts.

"What else is in here?" asked the eight-year-old, returning to the drawers.

Amy looked at the door. Setting down one of her cases, she placed her hand on the handle and opened, knowing that Tails would be in at the time. Not seeing him in the living room puzzled her, until she glanced up the stairs and saw her door was open. Sneaky Tails, she thought with a chuckle. She'd give him a right good hiding once she got a hold of him.

Said sneaky fox was currently looking himself over. He had found some pink stockings that matched Amy's underwear, and saw that he looked really good in them. Tails, deciding to have a little fun, blew a kiss to his reflection, before pulling up a chair and sitting in it, crossing his legs like he'd seen Rouge do many times.

Amy peeked her head in the doorway, only to be greeted by the sight of a young fox, sitting girlishly in a chair, wearing her clothes, and fluffing his hair in an extremely feminine manner.

"TAILS!?" cried Amy, causing the cross-dressing fox to turn around in horror.


	3. Amy's Judgement

Tails sat obediently in th chair, still in Amy's clothes. Said hedgehog was currently pacing the length of the room, her arms folded and an angry look on her face. She stopped and looked Tails right in the eyes.

"So..." she began. "You like wearing my clothes do you?"

"No! Amy it's nothing like that!"

"Why should I trust you? I told you not to go into my room didn't I? And you did just the opposite."

Amy leaned in closer. "Why did you do it?" she asked, her face softening slightly. "Do you like wearing girl's clothes?"

"No!... well, a little, but that's not why I wore them!"

"Then why did you?"

"Well, I was just curious to see what it felt like. I mean, why should girls get to wear boy's clothes but not the other way around? I just wanted to see what was so special about it."

Amy contemplated this. Looking over Tails, she saw he did look really cute in her clothes. Originally, she was going to beat him with her hammer, but with a devilish smirk, she decided to make the punishment fit the crime.

"You wanted to see what you're missing out, huh?" she asked with a voice laced in venom. "Okay, then. I'll make you a deal: you will come around for the times you would have while I was away, until my vacation would have ended. That means for the next four days, you will come around for five hours. And you must do exactly what I say."

Tails gulped, and simply nodded his head "Okay, just let me grab my stuff." However, as he bent over to pick up his shoes and gloves, a flash behind him caught his attention. He spun round to see Amy with her camera.

"Amy!" Another flash. tails was horrified. Now the sadistic hedgehog of pinkness had a full body pic of him in her undies, and another of him bending over, giving a good view of his rear.

"Just a little thing to guarantee you'll be round. Now come here tomorrow at 12 oclock, or everyone will see what a pretty lady you make!"

Tails had no choice. He nodded and bent over again.

"Wait." said Amy, glancig at the clock. "We still have a couple of hours left."

Tails could only watch as Amy walked over to her closet. "You wanna see what it's like to be a girl? Well, prepare to find out, _Melissa!_"

* * *

Well, that's Chapter 3. If anyone wants to see Tails in any particular outfits, or has any ideas that i could put in the story, tell me them in a review. Any help is greatly appreciated. 


	4. Twin Sisters?

Thanks everyone, for the _two_ outfit requests I got. Blake the Dog, you can expect plenty of skirts, and R0cknR011, I won't implement your idea in this chapter, but you inspired me, so it will happen, but not in the way you think (Amy won't make Tails go outdoors like that unless he refuses to follow her orders.).

* * *

Tails, who had been rechristened "Melissa" by Amy, sat anxiously in the chair Amy had caught him in, his twin tails twitching as he watched the pink hedgehog in front of him rummaging around in the cupboard. Amy could get a clear shot of her underwear, but he daren't say anything.

"A-ha!" cried the female hedgehog, causing Tails to jump. Amy turned around, and handed Tails a pair of black high heels. "We'll start with the basics. Slip these on, sweetie, and let's see how well you can walk in them."

Tails did as he was told, and immediately pulled the shoes on. He stood up, and wobbled a bit, not used to the weight distribution of heels, and would have fallen hadn't Amy grabbed his arm.

"Right, looks like we need to practice on that. Hold on." she returned to her weapons cabinet a.k.a. her wardrobe, and returned with a pair of red heels, matching Tails's black ones, and quickly swapped her boots for them. "Okay, now be sure that your heel touches the floor first, then your toe." she said, taking a step as she spoke to demonstrate this. Tails mimiced her, and and was able to walk quite good so long as he kept it slow.

"Good for a beginner, Melissa." commented Amy. "We'll work on that later. For now, it's time to get you dressed!" Tails gulped as Amy pulled out a spare red dress.

"First of all, since you look so cute in my underwear, you'll wear the same as me!"

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Amy stifled a laugh as she watched "Melissa" attempted to pull the hem of "her" dress down. "Okay, Melissa, sit down. I'll finish your makeover." The cross-dressing kitsune obeyed and walked over to the chair, which was miles easier in Amy's boots than those heels. As he sat down, Amy once again laughd at the fox's attempts to get comfortable.

"Melissa, cross your legs!" she laughed, and as much as he hated it, Tails did so. "Okay, now close your eyes and don't open them until I say so." Once again, Tails reluctantly followed her instructions.

With his eyes closed, Tails heard Amy returning to her wardrobe, and come back and place something on his head. The sounds of hair being brushed were heard, but Tails felt nothing. Then, strangely, he felt the object on his head be pushed down slightly, as if something was being used to hold it in place. Finally, he felt something brush across his eyelashes ever so slightly. Even blind, Tails had a pretty good guess what it was.

"Keep your eyes closed, sweetheart, and stand up." Tails conformed, and felt Amy lead him by the hand to somewhere. "Alright, dear, now place one arm around my shoulders..." Amy led his hand, "...and place the other's wrist on your hip." Tails did so. "Alright... open your eyes and smile!"

As Tails opened his eyes, a bright flash went off, and he found himself staring at a camera on a tripod. Amy ran over and checked the picture. "Oh, Tails, we look so cute!" she squealed, showing the child prodigy the back and failing to remember his girlish name.

Tails couldn't believe what he saw. The object that was placed on his head was a pink wig, that had been brushed to perfectly replicate Amy's style, complete with hairband to hold it in place. Tails suspicions about the eyes were correct: Amy had applied mascara, so he now had long feminine eyelashes.

"Apart from age and species, we could be twins!" laughed the rose-coloured mammal. She glanced at the clock. "Aw, Melissa, it's time you went home now. You'd better go get changed." she said, sounding like Cream when Vector and Espio came to pick up Charmy. Tails immediately dashed for the bathroom, and before Amy could say "How come he can run so fast in that dress?" Tails was back in his regular clothes..

"Well, I'm off." he said with enthusiasm. As he placed his hand on the handle, he heard Amy say "Don't forget, Mel: tommorrow, same time!" which made him cringe.

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Sonic took his feet of the coffee table, a habit which Tails had quickly picked up, and turned to Tails as entered. "So, how was it?"

Tails froze. "How was what!?" he asked, panicing. Had Amy phoned him when he was walking home?

"Uh, how was Amy's home? Everything still ship-shape?"

"Oh. Yeah, everything's cool over there." Tails didn't feel like talking at the moment. "Um... I'm gonna go work on the Tornado, okay?"

The cobalt hedgehog gave him a thumbs up. "No problemo, bu--" Sonic stopped midsentence, and got up and walked over to Tails, looking closely at his face.

"What is it, Sonic?"

"...Tails, are you wearing make-up?"

Tails immediately remembered. He forgot to wash of the mascara!

"Uh... erm... I was... checking out Amy's room, you know, making sure everything was allright, and I might of spilled some. Heh, heh." chuckled Tails nervously.

"Buddy, you can't spill mascara on your eyela--"

"Gotta go!" interrupted Tails, dashing for his workshop. Sonic stared as he left.

"Sometimes, I worry about him."

* * *

Heh, heh! Poor, poor, absent-minded Tails! Requests for outfits are still open, so if you have any ideas, leave them in the review.


	5. Leather, heels and Rouge?

Tails trogged along the street lazily. It was morning again, and he was on his way to Amy's for the second day of his feminization. Normally, he could have been there within seconds, but he was taking his sweet time, hoping to put off his inevitable torture. In around five minutes, he had walked as far as a regular person could walk in two, and as far as he could in five seconds.

Before Tails knew it, he was in front of Amy's door. Sighing heavily, he walked in, knowing Amy was expecting him.

"Melissa!" he heard our favourite sadist call out, causing him to cringe. "You're finally here!"

"No, Amy, I'm sitting on my couch, watching cartoons." he said, in a voice _dripping_ with sarcasm. _Dripping_, I tell you.

Amy, however, merely giggled at this. "You're so funny, Melissa! But anyway, it's time to get you dressed!" On the last word, Amy immediately grabbed Tails arm and pulled him up into her room.

She pulled out a pair of black thong panties, with white lace, and told him to go change into them. Upon coming out, she slipped a matching bra over his arms.

"Today, we're going to try something a little different. Just a little experiment." Oh no, thought Tails.

Amy pulled a large, black skin-tight bodysuit out of her wardrobe, and Tails's eyes widened at it. How long had she had _that_!?

For a moment, Tails breathed a sigh of relief as Amy placed on the bed beside him and returned to her closet, giving Tails the momentary impression she was just moving it out the way. Until she came back with a pair of breast forms and placed them in his bra cups, giving him a breast size to rival Rouge's.

Amy then slid the bodysuit on him, and Tails shuddered as the cold leather clung to his body. Things only got worse, however, when he saw Amy pull a pair of knee-high heeled leather boots, which Amy quickly slipped on him and zipped up. Amy stood back to admire her work, and Tails attempted to stand up. The combined attributes of a heavy chest and heels that made him taller than Amy mixed in the wrong way, and he would of fallen over had Amy not caught him.

"No, that look doesn't work for you, Melissa. Although..." Tails could practically _see_ the lightbulb turn on in Amy's head, and she quickly stripped the kitsuneof all but his panties, and Tails once again saw a glimmer of hope. But it faded when Amy pulled out a corset.

Watching as Amy slipped it over his head and tightened it, Tails immediately gasped for air upon feeling his lungs crushed. Amy finally slipped the breast forms back in.

Tails began taking shorter breaths, and watched as Amy reached into her clothes-cupboard, and he saw what she had been thinking. Amy now held the Rouge the Bat costume he had seen her wear last Halloween.

As Amy slipped the main bodysuit up, he saw that it fitted him much better than the last one did, and thankfully her boots had much lower heels. Amy looked Tails in the face.

"Melissa, I'm just going to grab my make up bag. I'll back in a jiffy, okay?" Before Tails could answer, Amy was already out the door.

Tails glanced at himself in the mirror, and saw to his horror, that from the neck down, he looked like an extremely curvy and well-endowed woman. He began to walk forward and gasped as he saw that the corset not only gave him a thinner waist and womanly hips, and the heels not only forced him to take smaller and more precise steps, but the two together made him sway his hips as he walked, like he had seen Rouge do so many times.

Amy came back at that moment and asked "Melissa" to sit down. Before she started, however, she mae an odd request.

"Melissa, cross your legs and place your hands on your knees." Tails looked at her strangely, but complied. He closed his eyes as Amy worked away, and finally, Amy told him to open his eyes and moved out of the way so he could see himself in the mirror. But he didn't see himself.

In the mirror sat a young vixen, her eyes a light blue colour that was complimented nicely with the cyan eye shadow she wore, and her eyelashes lengthened and darkened by her black mascara. Her lips were covered in a light pink lipstick, the colour matching her heart shaped breastguard and the hearts on her toes. A black bodysuit emphasised the lovely ladylikecurves she had, and a pair of elbow length gloves gave her an air of sophistication and elegence, that was contrasted by the knee high boots' somewhat slutty vision. Her stance, seated on a chair with her legs crossed and hands resting on her knees, made her look mature and patient, like a secretary waiting to be interviewed. There was no denying it; this vixen was beautiful.

Tails realised at that minute just how feminine Amy could make him.


	6. Acceptance

Behold, Chapter 6! I would have had this up earlier, but logged me out _just _as I hit the save button!

To Alex Warlorn and BoomTheHedgehog, who mentioned nightmares, I have been planning to incorporate a nightmare scene, but I've yet to figure out how. And R0cknR011, that is an excellent idea! I can't believe I didn't think of that! Thanks a lot!

Alex, I've seen that comic on deviantART, and it was funny (Simpsons fan!) Boom, I _will_ include your bikini idea, just not yet. And Dark Fox Tailz, I never thought about a sequel, but I don't see what's wrong about Amy dressing like a boy. But thanks for having so much faith in me!

* * *

"Oh!" cried Amy, suddenly realising something. "I almost forgot!" 

She rushed to her wardrobe, and pulled out a white wig, the styling of which Tails recognised as Rouge's. Amy didn't wear _that_ on Halloween. When'd she get it?

Amy shoved the wig onto Tails' head and pulled out a hairbrush from wherever-she-keeps-her-hammer and began to fix the hair until it was an exact replica of Rouge's.

"Okay, stand over there Melissa!" ordered Amy as she picked up her camera. 'Melissa' did as 'she' was told.

"Right. Now, lean forward a little bit, place one hand on your knee, and the other's wrist on your hip." instructed Tails' pink-furred tormenter, and she snapped a pic.

Several poses followed, including one where he made the 'bring it' gesture with one hand and the other on his hip, one where he placed one hand against his thigh and pointed daintily, even one where he looked over his shoulder while doing a "sexy walk." And the worst part was: she made him smile seductively throughout the whole thing.

Amy giggled as she looked over her pictures of 'Melissa.' "Oh, Melissa, you're so cute!" she squealed. Tails, on the other hand, had collapsed onto the bed. he was dressed like a girl, the high heels were killing him, and he still had two and a half days of this torture to go.

Tails made his decision. There was no way of getting out, so he might as well accept it. For the next 2.5 days, he was Melissa.

* * *

Yeah, I know it's short. But here's a bit of trivia/contest for you!

The four poses I mentioned Tails doing while wearing Rouge's clothes are actual poses she does in the official artwork. If you can tell me where they are all from, I'll let you pick the next costume/event for the next chapter.

I'll give you a clue: one of them isn't from a game.


	7. From Tails to Melissa

I am terribly sorry for the long wait. I've been really busy. Anyway, in regards to the poses thing I was doing, most of you got it right. But, Pheonix Wingz got it first. Ergo, he's won so his requests (Tails wearing Cream's outfit and Amy taking Tails shopping) will be done, though I hope he/she doesn't mind them being separate.

I also have to point out now, that I'm Scottish, hence why I was using the British terms in the first couple of chapters. But, I've stopped my denial; Sonic is American in the English games and I've come to grips with that.

Anyway, ON WITH CHAPTER 7!

* * *

Tails calmly watched Amy running back and forth between the bed and the closet, laying out his next outfit. Amy had already changed him out of his Rouge costume, and he was sitting there wearing nothing but the underwear. 

He took a glance at what they were, and recognised them instantly: an orange dress with a white collar, white socks, yellow and orange shoes, and white gloves with buttons on the cuffs. Tails sighed, having resigned to his fate, as he saw that she was going to dress him up in Cream's outfit.

"Found it!" his tormentor's voice rang out, as she returned with a blue ribbon. "Now give me your foot, Melissa."

Tails raised his foot, allowing Amy to slip the white sock on. Before Amy could tell him to, he raised his other foot. Amy smiled and slipped the other sock on, before Tails stood up, ready for the dress.

"Wow, Melissa." said Amy with a smile. "You seem to be enthusiastic!"

Tails forced a smile. "...yeah."

Apparantly not noticing the uneasiness in his voice, Amy beamed at him and picked up the dress, but after a moment's hesitation, handed it to Tails rather than putting it on him.

"Here you go! I'll let you put it on yourself."

Tails took the dress uneasily, as Amy headed to the door. "If you have any trouble with anything, I'll be in the living room!" she said with a smile.

Tails looked at the garment in his hands, and slipped it up over his head before pushing his arms through the armholes. He then slipped the shoes on, and clipped the gloves. He glanced at himself in the mirror, before picking up the ribbon and tried to tie it in the way Ceam always had it. However, it proved too fiddly, and he began to leave the room to find Amy, trying his hardest all the while.

Amy looked up, noticing Tails trying to tie the ribbon.

"Trouble, Melissa?" she asked as she got up. "No problem, I can get it!"

She walked over to Tails and did the ribbon expertly. "There you go, Mel! Now then..." she took a step back to see Tails in all his feminine glory, and let out a squeal.

"Oh, Melissa! You look great dressed as Cream!" Suddenly, a _look _came over Amy's face. The kind of look your sister gets when you've lost a bet with her. Yeah, _that _look.

"In fact..." she said, as a smile crept over her face. "...in fact... come with me!" and with that, she immediately grabbed Tails and dragged him back to her room.

What followed next was a blur for Tails. Next thing he knew, he had been stripped of his Cream outfit, and was standing in front of Amy wearing nothing but a simple white bra and panty set. Amy handed him a white tanktop and a pair of jeans with a floral pattern on them.

"Put these on, Melissa! And I've left some shoes out for you, so you can wear them when you're done." she said, as she left.

Tails, doing as he was told, pulled the tanktop on, followed by the jeans. He glanced over at the chair in the corner, and saw a pair of black Mary-Janes. Those must be for me, he thought as he walked over and put them on.

Just as he was doing the last buckle, Amy returned, carrying a red handkercheif and a brown wig. He began to get up, but Amy ushered him down.

"No, don't bother getting up! Just close your eyes!"

Tails shut his eyes, but not before catching a glimps of Amy picking up a brush. He felt Amy placing the wig and brushing it, and then he felt her... tying it? He felt something soft brush over his face, before a loud "Okay, open your eyes!"

Tails opened his eyes, and Amy directed him to the mirror, and he saw what she had done. Tails was now a brunette, with his hair now tumbling down his back. The handkerceif had been tied into it, giving him a hairstyle similar to Launch's from Dragon Ball. Finally, Amy had applied some mascara and blush to his face, giving it a real girlish look.

Amy happily took his arm and slipped a black handbag (or purse) onto his elbow, completing the look. Tails had to admit, he was a very attractive girl.

"Um... Tails?" he turned to Amy, the source of the noise. "Do... do you remember how I promised not to take you outside unless you disobeyed me?"

Tails' face pailed, as he realised wha Amy ws saying. "Amy, no!"

"But Tails!" she cried. "You're so pretty! You have to show yourself off, I even did you up so much that no one will recognise you!"

Tails turned back to the mirror. He did look completely different...

"Where were you planning on taking me?" he asked.

"You know... Station Square Mall... to get you some clothes..."

"No." said Tails flatly.

"Oh, come on, Tails!" whined Amy. "Please please please please please please please please please please..."

"No!"

"...please please please please please please please please please please..."

"Amy, stop it!"

"...please please please please please please please please please please..."

"If I say yes, will you shut up!?"

"Yes. Please please please please please please please please please please..."

"ALRIGHT!" screamed Tails. "I'll go!"

"Yay!" 'yay'ed Amy, as she grabbed her jacket and handbag (or purse). "To the mall!"


End file.
